Journal Articles Chemistry - A European Journal Year : 2024

Enantioselective Synthesis of Benzodihydrofurans Bearing Axial and Central Stereogenic Elements

Abstract

The enantioselective synthesis of chiral compounds containing multiple stereogenic elements via a single catalytic step is a challenging process. In the presence of α‐chloronitrostyrenes and a chiral squaramide catalyst, C−C or C−N pro‐axially chiral 2‐naphthol substrates, featuring low barriers to enantiomerization, underwent a remote diastereo‐ and enantioselective domino Michael/ O ‐alkylation. It provided the desired benzodihydrofurans bearing two stereogenic carbon atoms and a configurationally stable C−C or a C−N bond, thanks to a high increase of the barrier to rotation upon dihydrofurannulation.
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hal-04890886 , version 1 (24-01-2025)

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Antoine Domain, Xiaoze Bao, Jean Rodriguez, Damien Bonne. Enantioselective Synthesis of Benzodihydrofurans Bearing Axial and Central Stereogenic Elements. Chemistry - A European Journal, 2024, 30 (69), pp.e202403374. ⟨10.1002/chem.202403374⟩. ⟨hal-04890886⟩
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